Asymmetric inverse-electron-demand 1,3-dipolar cycloadditions of cyclopentadienones and thiophene-1,1-dioxide with C,N-cyclic azomethine imines

被引：12
作者：
Chen, Chen [1 ,2 ]
Yang, Xing-Xing [1 ,2 ]
Zhao, Zhi [1 ,2 ]
Han, Bo [4 ]
Du, Wei [1 ,2 ]
Chen, Ying-Chun [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Sch Pharm, Educ Minist & Sichuan Prov, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Peoples R China
[3] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
[4] Chengdu Univ Tradit Chinese Med, Sch Pharm, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 36期
关键词：
Chelation - Synthesis (chemical) - Ligands - Phosphorus compounds;
D O I：
10.1039/d2cc01103d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The normal 1,3-dipolar cycloaddition between the carbonates of 4-hydroxy-2-cyclopentenones and C,N-cyclic azomethine imines can be switched to an inverse-electron-demand version under Pd(0) catalysis, by in situ generation of HOMO-raised eta(2)-Pd(0)-cyclopentadienone complexes. An array of fused heterocyclic architectures are constructed with high levels of diastereo and enantioselectivity, and diastereodivergent synthesis is well realised by tuning the bifunctional phosphine ligands. In addition, similar reaction with in situ formed thiophene-1,1-dioxide is compatible by using a chiral bisphosphine ligand, and the fused cyclic sulfone frameworks are afforded with high stereoselectivity.
引用
收藏
页码：5502 / 5505
页数：4
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